Sonos Play:5

You won't be able to get a multiroom Sonos setup for $500, but you get Dad a Sonos starter set with the Sonos Play:5, which comes in white and black (or step down to the Play:3, which retails for $100 less).
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Slingbox 500

For the Dad who's a sports fan and wants to catch his teams on the road, you can't beat the Slingbox 500, which allows you stream your home cable or satellite feed to mobile devices and computers.
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